The address comes on the heels of an eventful year in Portland, which in November became the first East Coast city to vote in support of legalizing marijuana.

The city is experiencing a development boom of hotels and market-rate housing, including the approval of a high-rise development in Bayside. It launched a new motto – “Yes. Life’s Good Here” – to mixed reviews, approved the redevelopment of the Nathan Clifford School into market-rate housing, and successfully advocated for the passage of a $100 million state transportation bond.

The speech also comes after what proved to be a difficult year for city government, which found itself defending controversial policies in court and before large crowds at City Hall. Homelessness rose to record levels, and the city lost a crucial grant supporting its Health Care for Homeless Clinic.

The city also took a hit during last year’s state budget process, losing millions in revenue.

Ethan Strimling, a political analyst and former mayoral candidate, said Brennan should set a clear direction for the city. Like the governor’s State of the State and the president’s State of the Union, the address is a way to highlight the past year’s successes, but it’s also important that it acknowledge mistakes and draw lessons from them, he said.

“Portland has been put back on its heels a little bit,” Strimling said. “Good leadership steps out and says we don’t have a perfect union yet and we need to get there. That’s what makes the really good speeches stand out.”

Brennan became the city’s first elected mayor in nearly 90 years in a citywide election in 2011. Prior to that, a ceremonial mayor was chosen by the City Council.

Portland’s mayor is not the chief executive of the city, with the authority to hire and fire staff. Instead, he works with the city manager on the budget and policies, appoints committees and serves as spokesman for the city, especially at the state level.

The State of the City, which is required by the City Charter, is one way for the mayor to publicly set a vision and specific policy direction for the city.

Tom Valleau, who served on the Charter Commission that recommended the city switch to a popularly elected mayor, hopes Brennan will focus on a few key areas, including policies that encourage affordable housing, and address homelessness as a regional issue, as well as ways to increase graduation rates among high schoolers and maintain a business-friendly environment.

Last year, Brennan concentrated on the positive accolades the city had received by numerous publications and he featured local musicians in a video about Portland. He discussed his Growing Portland initiative, which was described as a collaboration between research institutions and the public and private sectors. He also hinted at a major education initiative, which was unveiled last year as Portland ConnectEd. It’s not clear how much progress has been made on those initiatives or whether he will talk about them again this year.

“I’d love to know what progress has been made,” said Pamela Plumb, who served on the city’s Charter Commission.

It’s also unclear if Brennan will address a series of contentious issues that have swirled around City Hall in the past year, most of which involve First Amendment and development issues.

The council and Planning Board recently approved increased heights and development plans for the first of four 165-foot-tall residential towers in Bayside. Two new downtown hotels are nearly finished, and the former Eastland Hotel reopened in December after a $50 million renovation as the Westin Portland Harborview Hotel. Also, dozens of market-rate apartment units have been proposed or approved on Munjoy Hill.

Meanwhile, a decision to change the zoning rules to allow an office use inside the historic Williston-West Church was overturned by the Superior Court, which reviewed the decision on an appeal of West End residents.

Plumb said she would like to hear Brennan set a balanced vision for development. “It seems to me that is something the mayor needs to speak to and put into context,” she said.

The city has also enacted several new ordinances that prompted First Amendment complaints.

Residents packed the council chambers to protest the sale of Congress Square Park to a private developer, and then sued the city for denying a group of residents petition papers to protect the plaza and 34 other open spaces. The residents won in court, which was concerned about infringing on free speech, but the city is appealing the decision.

Citizens also took the city to court on free speech grounds over a ban on loitering and panhandling in street medians. A federal judge has yet to rule in that case.

And while it is not yet the focus of a lawsuit in Maine, the fate of a buffer zone preventing anti-abortion protesters from demonstrating outside Planned Parenthood’s downtown clinic hinges on a precedent-setting freedom-of-speech case before the U.S. Supreme Court. During oral arguments in that Massachusetts case last week, Supreme Court justices were skeptical that buffer zones were in line with the First Amendment. They’re expected to rule by this summer.

Mayor Brennan also was entangled in a few internal struggles with city councilors, who have been critical of his leadership in setting council goals and his consolidation of existing subcommittees.

Brennan and the city’s top attorney also claimed the mayor could prevent items from appearing on the agenda, but councilors reaffirmed their access to the agenda by refusing to change the council rules.

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